Phosphorus oxychloride → 4-Chloro-6-(4-bromophenyl)thieno[3,2-c]pyridine

HRID 1814496Notes

Reaction equation

HRID 1814496 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=O)[C:11]3[CH:15]=[CH:16][S:17][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:12]1[C:11]2[CH:15]=[CH:16][S:17][C:10]=2[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[N:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 225024536-(4-bromophenyl)-5H-thieno[3,2-c]pyridin-4-one

Product 1

HCID 225035574-Chloro-6-(4-bromophenyl)thieno[3,2-c]pyridine

Conditions

Temperature
100 °C

Procedure

6-(4-Bromophenyl)-5H-thieno[3,2-c]pyridin-4-one (4.87 g) was added to phosphorus oxychloride (30 ml), and the resulting mixture was heated at 100° C. for 3 hr. The reaction solution was evaporated, and to the resulting residue were added ethyl acetate and water. The organic layer was washed with water, an aqueous solution of saturated sodium bicarbonate and brine, and dried over magnesium sulfate. The solvent was evaporated, to give 4-chloro-6-(4-bromophenyl)thieno[3,2-c]pyridine.

Workup

  1. customThe reaction solution was evaporated
  2. additionto the resulting residue were added ethyl acetate and water
  3. washThe organic layer was washed with water
  4. dry with materialan aqueous solution of saturated sodium bicarbonate and brine, and dried over magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-495c886d53cc49c48b2a090a71ac7bf2
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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